Unexpected Sugar Daddy

"Are you ready?" Josephine asked from the walk-in-closet of my bedroom.

"Ready," I said, sitting in the room's sole armchair. Josephine emerged from the closet, completely worth the wait. She was wearing a red, silk negligee. It was entirely translucent and trimmed in white fur over her breasts and along the hem. She spun for me to reveal it had a white fur bow on the back across her shoulder blades and then flared out into a v-shape, exposing her back. She had donned a matching pair of red lace panties. Josephine had curled her auburn hair and applied what could only be described as blowjob-red lipstick.

"Merry Christmas, sir," Josephine said as she sauntered over to me, barefoot and ripe for the plucking. She knelt down between my knees and I took a sip of the old fashioned I had poured for myself before she escorted me up to my own bedroom.

"It's Christmas Eve," I corrected.

"Well..." she said as she started unzipping my pants, "I want to unwrap my present anyway!" I laughed at the cheesiness of the line.

"And a happy new year," I said. Josephine started stroking my cock while fixing her gaze on me.

"Speaking of," Josephine said, "What are your plans for New Year's Eve?"

"Are we comparing calendars right now or..." I trailed off and Josephine smiled.

"No I wanted to ask you out," she said, "There's an art gallery opening that's hosting a New Year's Eve party at the same time. One of my favorite artists is there."

"And you want me to come with you?" I asked.

"Yeah it'll be fun!" Josephine said as she squeezed my shaft to got me to full attention.

"You won't be embarrassed to have an old man on your arm?" She bit her teeth playfully and I recoiled at the insinuation she could bite and was about to have me in her mouth.

"No!" she said, "First of all: no. Second of all, having an older lover makes me mysterious and sexy in the art world."

"Fair enough," I said, "Sounds good to me. What do I wear?"

"Mmmmm," she said as she leaned forward to lick the underside of my shaft, "Blazer maybe? Black if you have it. What do you want me to wear?"

Before I could answer, Josephine sank her mouth down on me and began bobbing her head fast on my cock. I moaned in delight and my head rolled back over the top of my armchair.

"Fuuuuuuck," I said. My hands found the top of her curled hair and I could not help but think: It's beginning to look a lot like Christmas.

* * *

Precisely one week later I was in the same walk-in-closet attempting to put on my cufflinks. I was sporting a black blazer, crisp white dress shirt, and grey slacks for the evening. Josephine walked by and saw me struggling. She pulled up in front of me to take the lead in affixing my cufflinks and I got to peer down at her New Year's Eve ensemble.

For the art gallery opening my young concubine had squeezed herself into a black minidress with a swoosh of silver sequins from her left shoulder down to her right hip. The dress had small sleeves that wrapped around the tops of her shoulders for warmth, it was the depth of winter after all, but a few well placed slits in the dress exposed the flesh of her left hip.

As an expert in Josephine's petite frame I was confident she was panty-less for the evening. Her partially exposed hip and the skin tight nature of the fabric, with no panty line, all but guaranteed it.

She had added a pair of black stockings that accented her legs marvelously. Even though they went up to the tops of her thighs and ended in a visible lace pattern, her dress was so short you could see all of her stockings and an inch or more of exposed leg before the hem of her dress finally began. Her feet were tucked into fashionable closed-toe, black pumps with a silver bow on each toe strap.

"You look gorgeous," I said.

"So do you," Josephine replied as she finished inserting my second cuff link. Looking down at her I couldn't help but admire her eyes, her cheekbones, and the beautiful figure she had.

Ten minutes later we were in an Uber to the art gallery event downtown. The way Josephine's legs crossed and rotated toward me, how sexy they looked in her dress, stockings, and heels, I started to get hard in the back of the car but steeled myself to come to my senses so early in the evening.

A quick jaunt down the highway, along with maneuvers through the crowded downtown streets of New Year's Eve, and we were delivered to the "Incaendi Gallery." As Josephine exited the car I was able to glimpse that she was, in fact, going commando underneath her skimpy dress. In the caveman days I would have been within my right to drag her into the alley then and there, but I held it together.

We walked into the gallery. Incaendi occupied two floors of a renovated red brick storefront, it was a large open space with a few walls forming nooks and crannies for patrons. Close to 100 people had to already be inside. Small bartender stations were spread throughout the venue and a DJ kept a stream of electro-house music, and what I call "Jazztronica" playing throughout the space.

Josephine wrapped an arm around mine and guided me through the initial foray of exhibits. At the front of the gallery stood two pegasus-like horse sculptures in bronze. The horse portions were incredibly accurate, the wings were harsh geometric polygons but incredible to look at it. They were offered for sale at $50,000.

"Josey!" A woman called from just beyond a small throng of patrons.

"Professor!" Josephine answered. An eccentric woman bounded out from the crowd and embraced Josephine. She was wearing a purple and black gown of sorts and had bright white hair formed into a tall up-do on her head.

"I'm so glad you came darling," the new woman said, "You're going to love it!"

"Honey," Josephine said, "This is Professor Kowalski. She teaches my Contemporary Art Practice class." I could not help but notice it was the first time she called me, 'Honey.'

"I am the one who invited you!" Kowalski said, "She is one of the most promising students I have had in a long time I -" But what she was I never heard. The DJ came on the speaker system and interrupted all the ongoing conversations.

"Ladies and gentlemen," the DJ said, "Please give it up for Tanner..." The crowds roared with applause, I found myself politely joining in.

"Come meet him!" Kowalski said, pulling Josephine from my arm.

"Oh no I couldn't!" Josephine said. I nudged her to go, assuming this must be the artist she wanted to see.

"Go," I said, "I'll get drinks." Josephine nodded and mouthed the words 'Thank You' as her professor pulled her through the walls of bodies toward the entrance of the gallery. I found the nearest bartender station and waited at least ten minutes for the two glasses of wine I wanted.

Once I had the wine in hand, I ventured through the gallery through the crowds toward Josephine's last known location. The walls of the gallery were mostly covered in works by this Tanner.

He was a mixed-media artist. Most of his work was painting, but he had a few pieces that were abstract sculptures and objet d'art, while a single wall held three photographs he had taken of a horse. His paintings were impressive. They had large, contemporary lines in single colors, and within the lines themselves he had painted impressionist-quality scenes of nature. They were not my personal cup-of-tea but they were good. He listed one of his auxiliary pieces for $5,000.

Despite enjoying my self-guided tour of the gallery I was eager to get one of my hands back by turning Josephine's wine glass over to her custody. After a few minutes of casually wandering toward the direction Kowalski had taken her, I found my date for the evening talking to Kowalski and a man I could only imagine was Tanner himself.

He was tall and lean with dark, curly hair draped over his neck. Despite it being late December he was wearing a black t-shirt that had a highly stylized white graphic on the center of his chest and grey slacks with black converse. He looked to be maybe thirty-five. He was handsome in an alternative and youthful sort of way.

Kowalski was practically swooning over him and Josephine was giggling at whatever Tanner had just said. I decided to exude confidence, but I had to admit my first thought was that if I was not around this would be the guy Josephine would go home with tonight.

I pulled up behind Professor Kowalski and gently cleared my throat. Josephine and Kowalski turned at once and I handed Josephine her glass.

"This is the artist I was telling you about," Josephine said. I extended my hand and greeted him.

"Tanner, I presume," I said. "Your work is fantastic. Touch of impressionism." Josephine was beaming at me, perhaps because I was a suitable escort for high society events or maybe it was that I had bothered to look at the exhibit she had suggested for the evening.

"Modern impressionism," Tanner said, "I try to add some of the flair my peers have for geometry." Just after he spoke to me I could tell he was eyeing Josephine then sizing me up, wondering what our relationship was. I could hardly blame him. Any straight man, and most women, would have their eyes glued on Josephine that night.

"And I'm sorry, you are..." Tanner added.

At that moment the DJ clicked on his microphone and interrupted, "All right ladies and gentlemen, the dance floor is about to officially open. But before we get you out here I want to call our featured artist up to the microphone for a toast!"

Tanner smiled at me as if to say, 'Sorry - I gotta go.' And waiters swarmed in with champagne flutes for the gallery patrons. Moments later I found myself holding a glass of champagne in one hand and Josephine in the other, my left hand scandalously draped around her left hip and the top of her cute little ass. It was more possessive than I tended to get in public, but given how sexy she looked and the number of eligible men in the room I felt compelled to claim my territory. She leaned into it.

Once everyone had their flute in hand, Tanner spoke."Thank you for coming tonight, everyone," Tanner said, "I cannot help but think of the great beauty that stands before us." Tanner noticeably fixed his eyes on Josephine, to me it was plain he was flirting directly with her despite there being hundreds of other listeners. After his pause to look at my date, he continued, "Of course I'm speaking of next year. Of the future. We don't know what will come and that is what we live for. It's a state of mind I find beautiful and I hope you find it reflected in the work I share with you here. Happy New Year!"

Everyone raised their glass to the artist, most of the women were entranced by him. After I downed my flute Josephine turned slightly into me, with my hand still wrapped around her.

"Are you having a good time?"

"I am!" I said, "Are you?"

"Yeah," Josephine said, "You seem tense though..." We began walking through one of the partitioned areas that housed the the work of the other artists on display.

"Do I?" I asked, "No - maybe you're picking up on me watching Tanner flirt with you and undress you with his eyes."

Josephine giggled and slapped my chest, "Oh my god he is not undressing me with his eyes!"

"Oh is he blind?" I asked. Josephine gave me a flirty look that indicated she still refuted my claims. "Oh he's gay then."

"He's not gay," Josephine said. "It's cute to see you jealous..."

"Hmmm am I jealous or just observant?" I teased, my left hand dropped to squeeze her butt cheek playfully as we glided through the gallery.

"Well," Josephine said, "I am spoken for."

"Damn right," I answered. Something in my tone gave me away to her.

"You're jealous!" She said, rounding on me. In her skin-tight dress, stockings, and heels it was impossible to ignore her.

"Well... not jealous," I said, "But if you were single and here..."

"Ah," Josephine said, "The freshman dorm experience conundrum!"

"Something like that," I replied.

"I am not worried about what I'm missing," Josephine said, "But I might occasionally use you for your body to fill in the gaps of what I expected. It's not like I was flirting back!"

"Hmmm maybe a little!" I said. Josephine pulled me in by my tie until we kissed, she suddenly became ravenous to sink her mouth onto mine and it was clear she was getting turned on.

"Then I guess you need to teach me a lesson, sir," Josephine whispered into my ear. I chuckled a bit.

"Should I call a car?" I asked.

"We can't leave...the party's just getting started," Josephine said. She grabbed my hand and led me toward a staircase in the back corner of the gallery. Dozens of people were nearby us, and she looked around before pulling me into a hallway toward the gallery's bathroom. As we walked down the hall she tested the handle of a janitorial closet and, lucky for both of us, it opened without complaint.

Josephine pulled me into the closet and then spun on her toes to face me. The closet had the overpowering odor of pine-sol and dust but that did not stop either of us. In a flurry we began running our hands over each other while we made out in the janitor's closet. Every few seconds we could easily hear guests walking by on their way to and from the restrooms.

My hard on became evident through my pants, pressing into Josephine's stomach. She sank to her knees and unzipped me, freeing my member into the cool air.

"Feeling territorial, sir?" Josephine asked as she began dragging her tongue up and down the underside of my shaft.

"I am," I said, wrapping my hands through her hair. Only the light peaking through the bottom of the doorway and a small ventilation hole illuminated the scene.

"Well I'm yours," Josephine said, "Now show me." I pulled her face forward, my cock pressing past her lips and into her mouth. For what felt like an eternity I used Josephine's mouth and throat, she kept her hands submissively on my thighs. I thought about cumming in her mouth, but having been forced to watch her slender legs work beneath her skimpy dress all night, plus the knowledge she was completely naked under her dress, drove me toward more.

I picked her up from underneath her arms and spun her around until both of her hands were resting on the doorframe of the closet. With my raging member pressing in her, I lifted the material of her dress to reveal her bare ass. My right hand squeezed her tight cheeks and I ran my fingers up and down her smooth pussy. She was soaked.

Instinctively I pressed forward, burying myself in her, before I placed one hand on her left hip and one hand on her right shoulder to hold her in place. Once we were situated she spread her legs farther apart to take my massive girth. How she stayed balanced in her heels while I pummeled her was a mystery to me.

At one point her moans exceeded the volume I thought we could reasonably conceal in the closet so I covered her mouth with my right hand and started fucking her harder. Josephine moaned into my palm and her legs shook as I ravished her in the closet. The thrill of knowing we could be caught seemed to work wonders for her, because she came only two minutes later. Both of her heel-clad feet pressed against each other as I continued pounding my sugar baby.

"Tell me when you're close," Josephine whispered as my hands roamed over the front of her petite frame.

"Oh I'm already close, baby," I said.

"Then please cum in my mouth, sir," Josephine said, "I can't have you dripping down my legs!" I laughed a moment before sending three more desecrating thrusts into her.

"Get on your knees," I said. Josephine turned around and sank to the floor, her legs weak from our session in the closet. My tip found her face in the dark and I trailed down her nose to her lips, she devoured me whole and began massaging my cock with her tongue. In less than I minute I could feel myself reach the point of no return, and I squeezed her head as my orgasm took over.

Stream after stream of hot cum filled Josephine's mouth and she dutifully swallowed my load, even deepthroating me twice as I spent myself. When I was finally done she let me fall off her lips with a small 'pop' and kissed the tip of my satisfied member. Josephine stood up and kissed me on the cheek.

"Happy New Year," I said.

"Happy New Year," Josephine replied, kissing my lips. "Now let's see if there are any other guys I can flirt with to get you stirred up! The night is young..."

I smacked her little rear as she opened the closet and peered out, confirming the coast was clear. We found our way to one of the nearest bars and secured a second round of drinks. Before he had paid, Professor Kowalski found us.

"There you are, dear!" The Professor said as she wrapped an arm around Josephine. "Where did you sneak off to?"

Josephine blushed a bit and, having been mid-drink anyway, took the opportunity to throw back a longer pull of her wine.

"Josephine wanted to show me a piece she thought I would love," I interjected.

"Ah, and did you?" Kowalski asked. I locked eyes with Josephine, who had gulped down her drink by then.

"The jury's still out," I said, "But I think so."